New functional group transformations can enable synthetic chemists to disconnect molecules in new ways, thereby enabling new synthesis strategies. Ideally such new technologies enable the synthesis of important molecules from untapped, perhaps more readily available, starting materials. In the right context, such methods can prove to be linchpin reactions for total synthesis and can offer new and more efficient routes to useful therapeutic agents. The proposed research will extend our fruitful studies on catalytic diboration reactions into a new range of stereoselective transformations. We will develop new strategies for constructing chiral organoboronates from simple starting materials and use these reactions to solve extant problems in synthesis.